Synthesis and anti-human immunodeficiency virus(HIV-1) activity of 3'-deoxy-3'- (triazol-1-ly)thymidines and 2',3'-dideoxy-3'-(triazol-1-yl)uridines, and inhibition of reverse transcriptase by their 5'-triphosphates.
- 1 January 1990
- journal article
- research article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 38 (9) , 2597-2601
- https://doi.org/10.1248/cpb.38.2597
Abstract
3''-Deoxy-3''-(1,2,3-triazol-1-yl)thymidines (5a, 6a, 8a, 11a, and 12a) and 2'',3''-dideoxy-3''-(1,2,3-triazol-1-yl)uridines (5b, 6b, 8b, 11b, and 12b) were synthesized as cyclic analogues of 3''-azido-3''-deoxythymidine (AZT) and 3''-azido-2'',3''-dideoxyuridine (CS-87) by the cyclization of 5''-trityl derivatives (1a, b) of AZT and CS-87 using .alpha.-ketophosphorus ylides and with acetylenic compounds followed by deprotection of the 5''-trityl group. It was hypothesized that the triazole nitrogen atoms could mimic and distorted azido group. However, no significant activity against human immunodeficiency virus type 1 (HIV-1) was observed with any of these compounds. 5''-Triphosphates (17a and 18a, b), prepared from 5a and 6a,b, were inactive against HIV-1 and Rauscher murine leukemia virus (RLV) reverse transcriptases.This publication has 20 references indexed in Scilit:
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